Gertrude's Siesta | 100% Private, 8-steps to Beach Path! 4-min Dining & Music! Snorkeling, Sunsets! Reviews, Deals & Photos 2025

Q: Is Gertrude's Siesta | 100% Private, 8-steps to Beach Path! 4-min Dining & Music! Snorkeling, Sunsets! pet-friendly?

Yes, pets are allowed at this property.

Q: Where is Gertrude's Siesta | 100% Private, 8-steps to Beach Path! 4-min Dining & Music! Snorkeling, Sunsets! located?

Situated by the sea, this apartment building is within 1 mi (2 km) of Crescent Beach and Siesta Key Beach. Point of Rocks and Siesta Key Marina are also within 15 minutes.

10/10 Excellent

Jenny N.

16 Dec 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family thanksgiving

We had a great stay here!

Stayed 4 nights in Nov 2024

10/10 Excellent

Alyssa A.

20 Oct 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best vacation

We had the best time here for a 3 night stay. Perfect location for the beach! The units were clean and was stocked well. The amenities were great. Highly recommend this place to all my family and friends!

Stayed 3 nights in Oct 2023

10/10 Excellent

anthony b.

30 Jul 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome

Awesome rental. Management was very nice and helpful. Most definitely will rent again.

Stayed 7 nights in Jul 2023

8/10 Good

Luke F.

15 Sept 2021

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Place for Friends Trip

The property was in a great location and had plenty of room for 22 of us. About a 3-4 minute walk from the beach as the beach access is right across the street from the main entrance. If you're looking for somewhere elegant or luxurious this probably isn't the place for you, but nonetheless it was a good property to spend a long weekend going to the beach.

Stayed 3 nights in Sep 2021

10/10 Excellent

Taylor H.

26 Dec 2021

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great spot for large group

Rented the whole Inn for a large group. Lots of beds. The outdoor dining space was great for gathering. Ample cooking space within the units and small appliances needed to cook and serve were available which was nice. Everything was clean upon arrive. Great access to the beach and beach chairs were very nice to have.

Stayed 5 nights in Dec 2021

10/10 Excellent

Elise S.

14 Oct 2021

Liked: Cleanliness, check-in, communication, location, listing accuracy

Classic Florida

This place is very cool and convenient to the beach. There are no ocean views but it’s an easy walk across the street. The house has everything you need. Owner was very helpful and answered our questions immediately.

Stayed 4 nights in Oct 2021

10/10 Excellent

Robert C.

8 Jul 2021

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family reunion

The old man and the sea was great for a family reunion. We had 25 family members who came through across the week - 5 different families and we fit nicely in the Inn. The beach was very close and is beautiful. Checking in was easy except we didn’t receive the combinations to the rooms until the day we arrived. It would have been better to have emphasized that fact early on. All in all it was a wonderful reunion thanks to the place we stayed

Stayed 6 nights in Jun 2021

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10/10 Excellent

Stephen P.

18 May 2022

Great for family gathering

Stayed 3 nights in Mar 2022

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Ricardo U.

18 May 2022

Great place forlarge groups

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: My family rented out the entire property for several days. It fit us perfectly and with having the separate units, gave us a space to retreat and have a separate space for each family. I love my nieces and nephews, but there are a lot of them so some "private" space is nice, The eating area was great and we brought some extra tables and chairs for our large group. It is nice to be able to eat all together. And the grills provided were excellent for large groups. Will definitely keep this property on our family's radar for future stays. Thank you!

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Michael M.

22 Jun 2022

Wonderful Trip

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great stay. Fantastic location.Two quick suggestions: 1. My Mom stayed in the Poor Boy & due to its proximity to the laundry room, her room had quite a few mosquitoes in it. They seem to swarm in the laundry room. 2. All the provided umbrellas have a pointed bottom at the base & what is really needed are the augur or corkscrew-type bottoms to better secure the umbrella bases.Thank you.

10/10 Excellent

Kiki A.

18 Aug 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Family Reunion spot!

Perfect fit for our group!! We rented all 5 units to accommodate group of 22. Having the entire place allowed us to take full advantage and enjoy all the areas for breakfast to late night gatherings. The owner & management team were incredibly responsive to requests. Tons of toys to use on-site and at the beach... we used the kayaks, the lawn games, the bicycles etc. There are plenty of chairs and umbrellas and towels. You really can show up and relax! We catered group dinners & cooked a full on BBQ on the two large propane grills. A person in our party was able to visit the location ahead of our visit so we knew exactly what the place looked like and it matches the pictures. Rooms are comfortable and had everything we needed. We'll stay here again or visit another of the owner's property for our next family reunion.

Stayed 3 nights in Jul 2022

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Danielle W.

18 May 2022

A perfect big group vacation/birthday celebration place to stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had the best time at this rental. We rented the whole place for my husbands 50th. The outdoor conversation areas were even better in person. It exceeded my expectations the units all having their own little living space made it so nice. People could wake up at their own pace come too with out anyone knowing or caring. The place was well stocked with all the beach supplies needed! The beach was beautiful. The sunsets out of this world!!! 22 people 18 were couples. We had beds to spare but I think we maxed out on couples. More singles could have stayed no problem. We didn't even use all the sofa beds. The lights outside made it magical at night for us to all hang out. We all can't wait to come back and we will! My only think I would mention were the beds could be upgraded. That said it wasn't something that would keep me from coming back

Stayed 4 nights in Dec 2021

10/10 Excellent

Paul K.

7 Aug 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

The ideal family reunion spot

We had folks fly in from all over the country and this amazing property had room for everyone, several great communal hang spots, and everything we needed to have a hassle-free stay just steps from a gorgeous beach. We hope to be back!

Stayed 4 nights in Aug 2023

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Rick L.

18 May 2022

Had a great time.

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We came down with 22 High School seniors along with 8 parents. We had plenty of room for everyone along with room for entertainment. The location was excellent, close to shopping and the beach for the kids. I would recommend this to anyone going to the Sarasota area.

10/10 Excellent

Lisa H.

20 Jul 2021

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful location

We had a wonderful experience at Old Man and The Sea!! Our family and friends rented the entire property for a senior trip for our boys. The property was clean and the location was phenomenal!! Communication for questions and comments was answered in a timely manner and Dan and Matt were very helpful! We would rent this property again.

Stayed 7 nights in Jul 2021

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Gertrude's Siesta | 100% Private, 8-steps to Beach Path! 4-min Dining & Music! Snorkeling, Sunsets!

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